2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 89768053, compound

HRID 591527Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:24])[CH2:4][C@H:5]1[C:9]2[CH:10]=[CH:11][C:12]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:17]=3[Cl:23])=[CH:13][C:8]=2[O:7][CH2:6]1.C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3](=[O:24])[CH2:4][C:5]1[C:9]2[CH:10]=[CH:11][C:12]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:17]=3[Cl:23])=[CH:13][C:8]=2[O:7][CH:6]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a mixture of methyl((3S)-6-((2,4-dichlorobenzyl)oxy)-2,3-dihydro-1-benzofuran-3-yl)acetate (367 mg) in toluene (5.0 mL) was added DDQ (272 mg). The mixture was stirred at 80° C. for 17 h. After cooling, the insoluble material was removed by filtration and the filtrate was concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexane) to give the title compound (263.6 mg).

Workup

temperatureAfter cooling
customthe insoluble material was removed by filtration
concentrationthe filtrate was concentrated in vacuo
customThe residue was purified by silica gel column chromatography (EtOAc/hexane)

Sources & evidence

ORD record: ord-cd2306715aae4e2db22834f9a8d1c332
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09238639B2

Reaction notes

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